What I’ve Learned from Sleeping with (a Lot of) Married Men

What I’ve Learned from Sleeping with (a Lot of) Married Men

I’ve always been pretty unapologetic about the fact that I sleep with other people’s husbands, boyfriends, and fiancés and will quite possibly do so again. The way I see it, what other people choose to do within (or outside) the confines of their own monogamous unions is no business—and certainly no responsibility—of mine.

sex at 26

The first time I ever had sex with a married man, I was a 21-year-old senior in college and he was my first-ever sugar daddy. You just slept with someone’s husband, I thought to myself the next morning, taking an Uber back to campus from one of eastern Connecticut’s sprawling casinos that rise out of the farmland like shining mini-metropoles. I think you are supposed to feel something. But all I could feel, hungover in the backseat of a car that would get me back to school just in time for my first class, was the sharp thrill of the illicit, and a faint, sickly gleam of satisfaction in the knifelike knowledge I’d just acquired: that I would never again have to worry about being enough for a man because there would never be any such thing.

I felt I had discovered an important if uncomfortable truth, one that made me feel smug and superior if also secretly scared and disillusioned—like a kid who just found out Santa Claus isn’t real. I’d only slept with one married guy, sure, but somewhere in the darker corners of my slick, shrewd cynic brain, I’d already begun to suspect that everyone cheats—and by “everyone,” I of course mean men. This night confirmed it: If he isn’t cheating or he hasn’t yet, then he wishes he were or he will be someday.

I wrapped myself up in this realization like a flag, flattered that I knew something my girlfriends would eventually learn the much harder way. I was more acutely aware than ever, of course, that it could still happen to me—that I may one day find myself on the other side of this dicey dynamic I’d entered into. Still, I was comforted by the knowledge that at least when my time came, I’d see it coming. I wouldn’t be blindsided the way women always seem to be getting blindsided by these inevitabilities.

It’s strange that I’m like this, by the way. I don’t have a convenient excuse—nothing that would hold up in a court of “Well, she’s sort of fucked up but it makes sense why.” My parents are still married, and, to the best of my knowledge, more or less happily so. As far as I know, I’ve never been cheated on myself. I’ve never even cheated on my own partner, when I’ve had one. Unless you count sexting or phone sex or meeting up in a dark, downtown bar where nothing happened but I wished it had, which you probably do.

I treat these men and my trysts with them like a vaccine. Take a shot of poison now, I tell myself, and it will save you later on.

Over the next few years, I added several more married-man notches to my belt. Many of them came to me the same way the first had—in sugar dating arrangements where it’s all but expected that one party is either “Married But Looking” or lying. Others stumbled across my path through different though no less cliché means—a workplace affair here, a DM slide there (on LinkedIn, of all places). I wasn’t necessarily seeking them out, per se, but once you’ve been baptized in the faith of Other Womanhood, I swear the cheaters can smell it on you.

But enough about me, what about the other woman? Or, rather, The Woman—the one at home checking her phone while I’m out fucking her husband or boyfriend or fiancé in bed at the St. Regis or bent over a bathroom sink at the Standard. Don’t I feel sorry for her? Or jealous of her? These are the questions I get from friends who listen to my sordid tales and quietly reassure themselves this kind of thing would never happen to their own relationships. And the answer is yes. And no. And sometimes—it depends. It depends whether you can reasonably assume she’s simply accepted her end of the bargain and agreed to look the other way—she gets the summer house on some old-moneyed stretch of coast and the 2.5 kids and is probably relieved enough that someone else is fucking her husband so she doesn’t have to—or whether she’s throwing tan, toned arms around him and sporting a shiny new diamond ring in an Instagram post you’ve looked at too many times. It depends whether you’ve just met up with him in a discreet hotel on a Wednesday night where he breaks the big news that he’s about to become a blushing groom to the woman he’s been cheating on with you for some four years and you leave feeling gutted in a way you didn’t know you still could.

Lately, some half-decade of married-and-otherwise-taken-men later, I’ve begun to wonder if I’m just poisoning my own well.

But even then, waiting for the N train too close to midnight and feeling stupidly, pathetically sorry for myself, I still felt safer on my side of this thing. I knew I’d rather be the one weeping on a subway platform than the one he’s slinking home to smelling like my Chanel Chance. Because every time you are the other woman, it comes with the reminder that you could just as easily be The Woman—even the ones with immaculate abs and sparkling résumés who have it all. And more than I crave the comfort and stability of long-term partnership—the status boost of split rent and shared last names and smiling vacation photos—I’m afraid of looking stupid, of some woman whose nudes are hidden in a password-protected app on my fiancé’s phone staring at my massive diamond and matching grin in an Instagram engagement announcement and seeing straight through it.

So I treat these men and my trysts with them like a vaccine. Take a shot of poison now, I tell myself, and it will save you later on. Then at least I’ll see it coming. At least I’ll be prepared.

I once tried to explain this to a man who, to the best of my knowledge, had never cheated on his wife of 20ish years. I told him that what I do is “preventative cheating.” Someday, I know (read: fear), I will be The Woman, so I’m getting my revenge on the future men I’ve decided will betray me now while I’m still young and can do it more easily.

“Sure, but it’s not ‘preventative,’” he pointed out. “He can still cheat on you.”

“Fine. Preemptive, then,” I conceded.

Sometimes I wish I could throw it all back up, all these things I’ve learned about men and marriage and monogamy from this side of them.

I used to take a certain kind of pride in proving my own worst fears right in this way, in making good on my most cynical beliefs. I used to like kicking the rotten foundations out from under things. But lately, some half-decade of married-and-otherwise-taken-men later, I’ve begun to wonder if I’m just poisoning my own well for no reason. Maybe the sheen is finally wearing off of that gleaming, knife-blade thrill, or maybe I’m just getting old(er). After all, I always sort of assumed that at some point I’d have to switch sideshow well can the serial sidepiece life really age? Then again, maybe the inner romantic in my heart of Piscean hearts has simply started to question whether staring down the ugly realities I’ve convinced myself are The Truth is really worth its weight in cynicism and apathy. In any event, sometimes I wish I could throw it all back up, all these things I’ve learned about men and marriage and monogamy from this side of them. Maybe it is the truth, but maybe I don’t need to know it anymore. Maybe I’d rather put my sunglasses down, have a glass of something sweet and see it all half-full and rosy.

sex at 26

Kayla Kibbe

It’s an aggressively sunny Sunday and I’m having hungover brunch with the handsome (and single) surgeon I’ve recently started seeing when he asks me what this essay is going to be about. I surprise myself by not wanting to tell him. Suddenly, somehow, this ugly truth I used to delight in shoving in people’s faces and down my own throat seems misshapen and out of place. It doesn’t match my flowery sundress or the crush on the boy across the hightop table I can feel blooming quietly in my chest. I try to defer—he’ll just have to subscribe and read it himself, I say.

He tells me he tries to avoid reading too much of my stuff. “I like where we are right now,” he says. He means: “I don’t want to see the darkest corners of your soul. I don’t need to taste the poison in your brain.” And I can’t blame him.

“It’s about cheating,” I tell him. I glance down. I stir my Bloody Mary. “Have you ever done it?”

His answer is the same mix of omissions and qualifications that is everyone’s answer if they’ve been on earth long enough: No—well, sort of. Depends if you count x, y, or z. But for the most part his record seems pretty clean. He is very gorgeous and kind and normal. He is not married or old enough to be my dad. And sometimes when he rests a tan, warm hand on my thigh in the car, I find myself wondering what it would be like to love and be loved by a normal, kind, gorgeous person and not worry about someday becoming The Womanthe one exchanging vows with a man who’s sexting someone saved under a fake name in his phone or waking up next to an undergrad in an expensive hotel room.

It’s not that I feel any of the regret or remorse many people would probably like me to feel. If I had it all to do over again, I’d do it all the same—not only because affairs, poison though they may be, are sometimes home to breathless, shimmering moments that can look a lot like love in the dim light of a hotel lobby bar, but also because this knowledge, these brushes with uncomfortable realities, have been valuable in their own way. They’ve added texture and nuance to the way I experience the world and my place in it.

But sometimes, when I catch myself thinking Girlfriend Thoughts like, Do you want to come over and watch TV on the couch with my feet in your lap, I wish I could mute the lessons I’ve learned from these adventures in infidelity. I wouldn’t take it all back if I could, but I would maybe donate it to Goodwill or try to sell it on Poshmark, like a skintight dress that made me feel sexy and powerful getting drunk off someone else’s bottle service at 21. It served its purpose for a time, but I’m not sure it has much left to offer me. I’m not even sure it fits me anymore.

Headshot of Kayla Kibbe

Associate Sex & Relationships Editor

Kayla Kibbe (she/her) is the Associate Sex and Relationships Editor at Cosmopolitan, where she covers all things sex, love, dating, and relationships • She lives in Astoria, Queens and probably won’t stop talking about how great it is if you bring it up • Follow her on Twitter and Instagram

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